gamithromycin   Click here for help

GtoPdb Ligand ID: 13688

Synonyms: ML-1709460 | Zactran® (veterinary)
Compound class: Synthetic organic
Comment: Gamithromycin is a 15-membered macrolide (azalide subclass) antibacterial compound. It was developed for use in veterinary medicine.
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 14
Hydrogen bond donors 5
Rotatable bonds 9
Topological polar surface area 180.08
Molecular weight 777.04
XLogP 2.67
No. Lipinski's rules broken 2

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES CCCN1C[C@H](C)[C@H]([C@@](C)([C@@H](CC)OC(=O)[C@H](C)[C@H]([C@H](C)[C@H]([C@@](C)(C[C@H]1C)O)O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)O[C@H]3C[C@](C)([C@H]([C@H](C)O3)O)OC)O)O
Isomeric SMILES CCCN1C[C@@H]([C@H]([C@]([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@](C[C@H]1C)(C)O)O[C@H]2[C@@H]([C@H](C[C@H](O2)C)N(C)C)O)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)OC)C)CC)(C)O)O)C
InChI InChI=1S/C40H76N2O12/c1-15-17-42-21-22(3)33(44)40(11,48)29(16-2)52-36(46)26(7)32(53-30-20-39(10,49-14)34(45)27(8)51-30)25(6)35(38(9,47)19-23(42)4)54-37-31(43)28(41(12)13)18-24(5)50-37/h22-35,37,43-45,47-48H,15-21H2,1-14H3/t22-,23+,24+,25-,26+,27-,28-,29+,30-,31+,32-,33+,34-,35+,37-,38+,39+,40+/m0/s1
InChI Key VWAMTBXLZPEDQO-UZSBJOJWSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2R,3S,4R,5S,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-7-propyl-1-oxa-7-azacyclopentadecan-15-one
International Nonproprietary Names Click here for help
INN number INN
8754 gamithromycin
Synonyms Click here for help
ML-1709460 | Zactran® (veterinary)
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Gamithromycin
Other databases
CAS Registry No. 145435-72-9 (source: Scifinder)
ChEBI CHEBI:195437
ChEMBL Ligand CHEMBL2107342
DrugBank Ligand DB11416
DrugCentral Ligand 5548
GtoPdb PubChem SID 507750322
PubChem CID 59364992
Search Google for chemical match using the InChIKey VWAMTBXLZPEDQO-UZSBJOJWSA-N
Search Google for chemicals with the same backbone VWAMTBXLZPEDQO
Search PubMed clinical trials gamithromycin
Search PubMed titles gamithromycin
Search PubMed titles/abstracts gamithromycin
UniChem Compound Search for chemical match using the InChIKey VWAMTBXLZPEDQO-UZSBJOJWSA-N
UniChem Connectivity Search for chemical match using the InChIKey VWAMTBXLZPEDQO-UZSBJOJWSA-N